I just don't see how this works out profitably in the current market.

Hey Michael, Not sure which book you read about wholesaling, but here's the deal: wholesaling is mostly about sales and marketing.

I'd recommend reaching out to your local REI meet ups and see who the seasoned investors are using. 

The best method often depends on your specific circumstances, credit profile, and local market conditions.

I'm giving myself a year to learn all I can and save up a down payment for my first long-term rental in my local area.

the rents can be brought up to market value maybe of $5200 but that doesn't make sense either

In brief, the concept was to make lots that are City-owned available via a quit claim deed to residents or community groups within the specific neighborhood on the same block in order to stabilize communities through local investment. https://www.chicago.gov/city/en/depts/dcd/supp_info/large-lo...There were a few other historic land sale programs in addition to large lots.

A two car garage depending on your market is probably 15K-20K.  

@Elijah HouseholderCheck with your local planning department about permitting the building.

Why This Matters: For investors in multi-family properties, especially in today's real estate market, maximizing tax savings is crucial for maintaining profitability.